Scamfluencers - Leona Helmsley: The Art of the Steal Part 2

Episode Date: April 22, 2024

Leona Helmsley’s perch atop the world of Manhattan real estate is threatened by federal tax evasion charges. Her trial gives all the people she bullied a chance to hit back. With her dirty laundry aired out for all to see, the Queen of Mean is served her just desserts. But as she soldiers on without her beloved Harry, Leona will have terrible trouble defending her riches, and her heart.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Wondery Plus subscribers can listen to Scamfluencers early and ad free right now. Join Wondery Plus in the Wondery app or Apple podcasts. This is the finale of our two-part series on Leona Helmsley. I promise you, if you don't listen to part one, you're missing out. So go catch up and then meet me back here for more. Sarah, what do you remember about our last episode about Leona Helmsley? I remember that this woman was like the blueprint for girl bosses of today. She became this renowned hotelier and was kind of known to be a little bit of a bitch.

How do you think our saga with the Queen of Mean will end? I think she will repent for being unkind to her workers and poor people, and, you know, everything will end up okay. You're an optimist. Well, Sarah, there's no way to prepare you for where we're going. Suffice to say, it's fewer fur stoles and caviar dinners, and more the early fall of capitalism. Should be fun! and more the early fall of capitalism. Should be fun.

It's a chilly April morning in 1988. It's been more than a year since the New York Post published explosive allegations about Leona and Harry Helmsley dodging their taxes. Since then, the Post has published dozens more articles digging into the power couple's sketchy finances. Now, they're in the back of a stretch limo driving to the attorney general's headquarters in downtown Manhattan.

Harry once owned this building, but now he's here with his wife to be criminally charged. Leona is 67 years old, but she looks much younger, with coiffed hair and perfectly applied makeup. She's wearing a bright red coat dress with brass buttons and white pumps. Harry, at 79, is still tall with a head of thin gray hair. Unlike Leona, his age has caught up to him. He's been suffering from serious medical issues, including a stroke.

He shuffles behind her, wearing a dark cashmere coat. Their bodyguards escort them through the crowd. Reporters hurl questions at them. Someone asks Harry what he considers to be his greatest accomplishment. It's meant to be a jab at a man whose life is rapidly falling apart. But instead, Harry hooks his arm in Leona's and says, marrying her.

Oh, my God. If I was a reporter there, I'd be like, thank you, sir, for this response that everyone will read and react to. Perfect soundbite. The couple has been charged with conspiring to defraud the government of $4 million in taxes by listing their personal shopping sprees as business expenses. They plead not guilty.

And two of their former aides have also been charged with helping them pull off the scheme. New Yorkers can't get enough of the schadenfreude. Here's an ABC report on the arraignment filed by local news guy Bill O'Reilly. Some New Yorkers are looking at the Helmsley case with amusement. A local nightclub is even throwing a party with the theme Free Leona. But it's serious for the Helmsleys.

They could go to jail for years. The Bill O'Reilly of it all, aside from that, that is pretty funny that she became like a meme before the internet. People being like, this is ridiculous and funny, let's throw a party. I could see that happening today. Yeah, probably. While Leona is used to the spotlight, but this is different.

The 80s have been a decade of celebrating greed, but the tide is turning against the rich and the shameless. Even the US District Attorney, a star lawyer named Rudolph Giuliani, is taking advantage of the moment to get good press. We all know Rudy as a bald, withered grifter with hair dye dripping down his face, but at this point he's a rock star prosecutor. He's 43 and recently gained national fame for securing convictions against eight of the biggest mafia bosses in the country.

At a press conference in front of his office, Rudy says he wants to make an example out of Leona and Harry. The timing of the return of the indictments is meant to underscore the deterrent principle and to remind people of their obligations to pay taxes. Leona's ruthless ambition gained her wealth and fame, but the pendulum of public favor is about to swing way, way back. The backlash against her will jeopardize her career, her marriage, and her freedom. Because Leona is about to discover that karma is almost as big of a bitch as she is. I'm Afua Hirsch. I'm Peter Frankopan.

And in our podcast, Legacy, we explore the lives of some of the biggest characters in history. This season, we delve into the life of Alan Turing. Why are we talking about Alan Turing, Peter? Alan Turing is the father of computer science and some of those questions we're thinking about today around artificial intelligence. Turing was so involved in setting and framing what some of those questions were, but he's also interesting for lots of other reasons, Afro. He had such a fascinating life. He was unapologetically gay

at a time when that was completely criminalised and stigmatised. And from his imagination, he created ideas that have formed a very physical, practical foundation for all of the technology on which our lives depend. And on top of that, he's responsible for being part of a team that saved millions, maybe even tens of millions of lives because of his work during the Second World War using maths and computer science to code break. So join us on Legacy, wherever you get your podcasts. Listen to top podcasts like How I Built This and Business Wars Early and Ad Free only on Wondery Plus. Wondery means business.

From Wondery, I'm Saatchi Cole. And I'm Sarah Hagy. And this is Scamfluencers. In our first episode, Leona Helmsley went from depression era dreamer to power executive. She rose to the top by intimidating renters, raiding employees, stiffing contractors, and protecting her bag at all costs.

Now it's the late 1980s, and her name has become synonymous with money and glamour. But the idea of being queen seems to have gone to her head. And when her shady accounting practices are called into question, all the people she lied to or stole from or mistreated along the way will get their chance to strike back.

The queen of mean is facing a rebellion that may cost her everything. This is Leona Helmsley, The Art of the Steal, part two. This is Leona Helmsley, The Art of the Steal, Part 2. In April 1989, a year after her indictment, Leona is probably sitting in her penthouse having some of her famously scalding hot coffee. She takes a sip and unfolds a New York Post. She's likely not surprised to see herself on the front page. Ever since the Post broke the story that led to her indictment, they've continued to publish a flood of stories about the ongoing investigations.

But this morning's headlines are about a very different kind of threat. Sarah, can you describe this front page? Yeah, it's a classic New York Post front page, huge, huge text on the front. And it says, Trump lashes Leona, calls her disgrace to the industry. And there are two photos, one of Leona, calls her disgrace to the industry. And there's two photos, one of Leona, one of Donald Trump.

I mean, knowing what we know now, this is so funny and obviously a way to like be in the news, but I feel like then people would have been like, okay, go off. Someone's saying it, another rich person saying it. Okay. Well, you may remember from our last episode that a young Donald Trump used to come to Harry's birthday parties. Leona and Trump have always had a frenemy-type relationship, but it became a full-on feud about four years ago when Trump bought a hotel from the Helmsleys. He claimed Leona was so cheap that she wanted him to pay for the stuffed animals in the lobby ice cream parlor. And with those shots fired, Leona went scorched earth.

She cut ties with anyone in her life who had any connection to him. Like Joyce Bieber, the advertising whiz who created the Queen of the Palace campaign. Leona fired her after learning she was in talks to make ads for Trump. But Trump only became more famous and more powerful. He published the bestselling book, The Art of the Deal, and even started floating the idea of running for Trump. But Trump only became more famous and more powerful. He published the bestselling book, The Art of the Deal, and even started floating the idea of running for president. All of this attention on Trump makes Leona even more enraged. Her most recent dispute with him is over a Helmsley property in Atlantic City.

Leona wants him to pay for it handsomely. Trump is so livid over her escalating prices that he writes her a letter, which becomes the basis of that New York Post article I just showed you. Sarah, can you read one of Trump's quotes from it? It says, When God created Leona, the world received no favors. Without the veil of Harry Helmsley, you would be a non-entity. Oof.

That is so mean and could have been straight from his tweets. He's kind of always been straight from his tweets. He's kind of always been the way he is. Yeah, he has not changed at all. And when asked for comment, Trump twists the knife, calling Leona a quote, disgrace to the industry and disgrace to humanity in general.

But Leona declines to comment, not by choice, she's under a gag order from the federal judge. And she's dealing with a major issue behind the scenes, Harry's deteriorating health. Just days before their trial is set to begin, the court makes a stunning decision. It says that a series of small strokes and other medical conditions, including dementia, have left Harry unfit to stand trial. So the charges against him are suspended indefinitely.

Later, Leona says that Harry wouldn't have physically survived a trial. But the decision means she'll have to face a jury of New Yorkers all on her own. The day after her 69th birthday, in July 1989, Leona arrives at the federal courthouse in Manhattan. She's wearing a checkered blouse that's power clashing with a striped coat. The courtroom is packed with spectators. The prosecuting attorney starts things off by saying that the Helmsleys used their position, their power, and their privilege to avoid paying income tax.

He says the evidence will show that Leona and Harry are arrogant and greedy and that they believe they're above the law and that Leona used her company as her quote, personal piggy bank. Then it's time for Leona's lawyer to lay out his opening argument. And Sarah, you have to read what he starts with.

He goes, they will bring in witnesses to paint Mrs. Helmsley in a way that you will hate her. She has no patience with those who fail to live up to her expectations. But I don't believe Mrs. Helmsley is charged in this indictment with being a tough bitch. I kind of understand this opening argument, get it out of the way.

Yes, we know she's terrible. However, that's not what we're talking about here. The facts of this case are, for the most part, undisputed. The Helmsley's charge renovations at Dunn-nellon Hall, their personal estate, to their business. And then they fail to list them on their personal taxes. The prosecution has the evidence to prove it. They fill the courtroom with filing cabinets, cardboard boxes, and grocery carts full of Leona's doctored invoices.

Leona's lawyer claims that her intention wasn't to avoid taxes. He argues that some Dunnellan expenses were legitimate business expenses, and puts the blame for messing with the invoices on the former aides who are charged alongside Leona. Over the next couple of weeks, the prosecutors produce evidence that Leona and Harry were charging tons of personal expenses to their company. And these expenses are wild, even by scamfluencer standards. More than a million dollars to build a pool enclosure with a marble dance floor on top, half a million dollars in jade art objects, over a hundred thousand dollars for an indoor-outdoor

sound system, and a $45,000 silver clock in the shape of the Helmsley Building. As the trial goes on, more than 40 witnesses testify about being personally victimized by Leona. Many of their stories are so outrageous that the courtroom breaks out into laughter. Steve Chang, the guy who helped get their sound system, testifies about being asked to falsify invoices. And a former housekeeper says that she once told Leona,

you must pay a lot in taxes. And she says that Leona responded with, we don't pay taxes, only the little people pay taxes. It's so funny because I feel like people who are rich this way try and find ways to avoid talking about that at all. Like they're not gonna straight up be like, no, I don't pay taxes, you idiot.

Only people like you do. You know, they have ways to hide this fact, but she's very open about it. Well, reporters cannot file their stories fast enough. And it's not just newspapers and tabloids that are profiting off this explosive trial. Other New York figures are using Leona's troubles to distract from their own.

That summer, New York Mayor Ed Koch's re-election campaign is floundering. So he starts talking about Leona at campaign events, calling her the wicked witch of the West. Shock-jock Don Imus nominates Leona as insect of the year. Even Carol Burnett says that if she still had her TV show, she would be doing impressions of Le year. Even Carol Burnett says that if she still had her TV show, she would be doing impressions of Leona. And obviously, Donald Trump still has plenty to say. When the business deal to sell him the hotel comes up in the trial, he gives a scathing quote

to the Los Angeles Times. Sarah, read it for me, please. Yeah, it says, I can feel sorry for my worst enemy, but I cannot feel sorry for Leona Helmsley. She deserves whatever she gets. I mean, it is really just a free for all on Leona. Like I know she's evil, but people really are enjoying going for her. Yeah, they really love to yell at her. And thanks to Leona's gag order, she still can't say a word to defend herself. All she can do is watch in horror

as the public image she has carefully constructed over an entire lifetime is torn to shreds. As the trial winds down, she has to stand by while her fate rests in the hands of the so-called little people she once dismissed. The trial lasts seven weeks, followed by five days of deliberations. On the morning of August 30th, the jury comes to a decision.

Leona sits in silence as the foreman stands and reads the verdict. She's found guilty of more than 30 counts, including tax evasion and tax fraud conspiracy. There are so many convictions that it actually takes the foreman nearly 10 minutes to read all of them. Leona lowers her head, and some reporters later claim that she has tears in her eyes. She's never been this low. She entered this court two months ago as the queen, and she's leaving as a felon. Because of his failing health, Harry isn't even at her side.

While Leona waits to find out her sentence, New York Post reporter Ransdale Pearson releases an unauthorized biography of her. He calls it The Queen of Mean. It contains all his reporting from the last two years, including interviews with her ex-husbands, her son's widow, and a boatload of former employees and contractors. Ransdale's reporting led to the trial currently roiling Leona's life, and his book popularizes the nickname that will follow her forever. Four months later, on a snowy afternoon, Leona is back at the courthouse for her sentencing hearing. She's wearing a black silk dress and a dark coat with a high collar. The room is packed with more than 200 people.

She faces up to $8.5 million in fines and more than a century in federal prison. That is so insane that she can face more than 100 years in prison. That is just crazy to me. I know, it's a long time. And meanwhile, nothing's really happening with Harry, I'm guessing.

Yeah, I mean, not really. Leona tearfully tells the judge, quote, I'm more humiliated and ashamed than anybody could imagine. She brings up the trauma of losing her son, Jay, and asks the judge not to let her lose Harry as well. And well, the judge is not really having it. He says that Leona's conduct was, quote, a product of naked greed.

And he sentences her to pay a fine of over $7 million, but only four years behind bars. Leona whispers, see what they've done to me? And Harry holds her as she sobs. Leona is released on bail pending an appeal. But if she found little pity inside the courtroom, then outside is even worse. Here's how CBS Evening News reports on the scene. The judge said she had become a lightning rod for public vilification, and that was clear outside as Leona Helmsley left the court to a chorus of jeers. Leona's lawyer is scrambling to try to get her a new trial.

And in the meantime, she'll have to plead her case in the court of public opinion. It's early February in 1990. Leona is sitting across from New York Post gossip columnist Cindy Adams. She's about to record her first TV interview in five years for the news show, A Current Affair. Now that the trial is over, she can finally speak to the press. Leona relaxes into her chair, looking forward to this chance to tell the country that she's

done nothing wrong. In fact, she says she has never cheated on her taxes. If anything, she overpaid. She looks Cindy directly in the eye and says that she is the real victim. I can't believe that the system in the United States of America has stopped working. It's one of many interviews Leona does. Speaking with the New York Daily News, she says that the Queen of the Palace ads worked against her in the public eye.

When asked about the very real possibility of going to jail, Leona simply refuses to accept it. She says, quote, It's impossible. It can't happen. The appeal can't fail. Then, in August 1990, not long after the start of the Gulf War, Leona spends more than 40 grand on a full-page ad in the New York Times. The ad features an open letter she's written to Iraqi President Saddam Hussein.

Sarah, I think you should read some of it. Okay, huge letter. It says, Dear Mr. Hussein, In your bizarre world where detention centers have become hotels and hostages have become guests, I can make one recommendation that I have never made in all the years I've been welcoming people. Mr. Hussein, it is time to check out. I ask that you release these hostages at once

and confront this conflict of your making without the human shields you now cower behind. What on earth? What on earth is this? What would compel her to do this? This is one of the most shocking things that you've shown me in an episode, because it's just so utterly bizarre. Yeah, this is a really weird look for her to be spouting her political opinions

and spending all this money while she's trying to overturn her fraud conviction. When a Los Angeles Times reporter interviews her about it, Leona assures him that her lawyer and her PR firm thought publishing this letter was a great idea. She says, They thought it was a wonderful thing to do. How did you ever think of anything so wonderful? You know what, I do believe that because I think they're like, listen, we got to pick

our battles with this woman. If she thinks she is spreading goodness to the world by paying for a full ad in the New York Times addressing Saddam Hussein about people he's terrorizing, then like maybe we should just let her if that's how she wants to show kindness. Well, regardless of the letter, the backlash against Leona continues to grow. A TV movie about her comes out in September. It's called The Queen of Mean, based on Ransdell's book. Meanwhile, her best friend of mine, Donald Trump, continues to trash her.

Donald and Ivana have announced they're splitting up. Sarah, can you read the reason that he gives publicly for the divorce? Yeah, he says, Ivana's level of arrogance has grown steadily worse in recent years. The bottom line is, I don't want to create another Leona Helmsley. Oh my God, that is so mean. Brutal.

Well, Leona is a big believer that all publicity is good publicity. But as her appeal date draws closer, she's about to see how her coverage in gossip columns measures up against her rap sheet. Hello, I'm Emily, one of the hosts of Terribly Famous, the show that takes you inside the lives of our biggest celebrities. Some of them hit the big time overnight, some had to plug away for years. But in our latest

series we're talking about a man who was world famous before he was even born. A life of extreme privilege that was mapped out from the start, but left him struggling to find his true purpose. A man who, compared to his big brother, felt a bit, you know, spare. Yes, it's Prince Harry. You might think you know everything about him, but trust me, there's even more. We follow Harry and the obsessive, all-consuming relationship of his life. Not with Meghan, but the British tabloid press.

Hounded and harassed, Harry is taking on an institution almost every bit as powerful as his own royal family. Follow Terribly Famous wherever you listen to podcasts or listen early and ad-free on Wandery Plus on Apple podcasts or the Wandery app. I'm Alice Levine and I'm Matt Ford and we're the presenters of British Scandal and in our latest series Hitler's Angel we're the presenters of British Scandal. And in our latest series, Hitler's Angel, we tell the story of scandalous beauty Diana Mosley, British aristocrat, Mitford sister, and fascist sympathiser. Like so many great British stories,

it starts at a lavish garden party. Diana meets the dashing fascist Oswald Mosley. She's captivated by his politics, but also by his very good looks. It's not a classic rom-com story, but when she falls in love with Mosley, she's on a collision course with her family, her friends and her whole country. There is some romance though. The couple tied the knot in a ceremony organised by a great, uncelebrated wedding planner,

Adolf Hitler. So it's less Notting Hill, more Nuremberg. When Britain took on the Nazis, Diana had to choose between love or betrayal. This is the story of Diana Mosley on her journey from glamorous socialite to political prisoner. Listen to British Scandal on the Wondery app or wherever you get your podcasts. In July 1991, Leona gets some relief. A federal judge upholds her tax fraud conviction, but demands that an appeals court revisit her sentence. Leona holds out hope that this could mean she'll face no prison time at all.

She's just turned 71 years old. Harry is in his 80s and still struggling with his health. He's managed to escape any consequences for his actions, but Leona's happy to be back at home with him, at least for the time being. Seven months later, in March, 1992, Leona is in front of a judge again. It turns out she's got to serve her four-year sentence.

Leona's hopes are dashed. She'll have to report to prison on tax day. I do wonder if they picked that as like a little in-joke. You know, like, hey, we could pick any day. Let's just make it tax day for her. Yeah, I don't know that the courts have a sense of humor, but I hope on this one that they did. Leona still can't comprehend how any of this could happen.

How she could be taken from her home, her hotels, her Harry. When she's sworn by reporters on the courthouse steps, she sticks to her story. I have done nothing wrong. I'm innocent. My only crime is that I'm Leona Helmsley. Oh, my God. I do love her voice. She sounds like Jack Donahue's mom from Dirty Rock. Yeah. I kind of think everybody does from that period of time in New York. Oh my God, I do love her voice. She sounds like Jack Donahue's mom from Dirty Rock.

Yeah. I kind of think everybody does from that period of time in New York. And you know what? Being Leona Helmsley is not a crime. She is correct. Technically true. While Leona is helped through the crush of the crowd by 10 federal marshals, the scene is so intense that she collapses.

As she's helped into her car, someone screams, kill the rich. She's later admitted to the hospital for high blood pressure and chest pains. Leona's lawyer rushes to file a motion for a new trial. While Leona waits, she does something much scarier than lecturing foreign dictators. She gets emotional.

She agrees to an interview with Barbara Walters for 2020. When Barbara arrives at Leona's penthouse, she finds Leona still in bed. Leona gets up, wraps a red robe around herself, and puts on house slippers. She agrees to appear on camera seemingly without makeup. They sit in the penthouse living room, which overlooks Central Park.

And Leona shares her turmoil with Barbara while dabbing her eyes with tissues. Barbara tells Leona that if her motion to get a new trial moves ahead, people will say she's getting special treatment because she's rich. And Leona fights back, saying that she is getting special treatment. If she wasn't rich and she wasn't Leona Helmsley, she would have gotten a slap on the wrist and then sent home. And then Barbara asks her what she'll do if she doesn't get a new trial. Why wouldn't I get a new trial? I'm entitled to something here, for $600 million in taxes. Surely I'm entitled to a little justice.

But no amount of courting public opinion will change the facts. Less than two weeks after the Barbara Walters interview airs, Leona's motion for a new trial is denied. Her fate is sealed. After so many years of treating life like a zero-sum game, this time she's rolled the dice and lost. Around 1 AM on April 15, 1992, Leona climbs aboard her private jet. She's carrying a lightweight bag. on April 15, 1992, Leona climbs aboard her private jet.

She's carrying a lightweight bag with some night clothes, underwear, and shoes, and wearing just one piece of jewelry, her wedding band. After a short flight and a long drive, she checks into a federal prison in Kentucky. Fun fact, this is actually the same place where Scamfluencer's alum, Julie Chrisley of Chrisley Knows Best is currently incarcerated.

Leona is searched and ordered to change into her new prison wardrobe, a blue shirt and pants. The warden at one point jokes that her work in the hotel biz may help her with mopping floors or folding bed sheets. That night, back in New York City, Harry orders that the lights of the Empire State Building be shut off. You know, at the end of the day, these two people are in love. That is so much more than a flag being half-masked. Well, after about a month, Leona is transferred to the Danbury Minimum Security Prison in Connecticut. That's where Scamfluencer's alum Teresa Giudice will later serve her time as well.

Leona's assigned a job giving up prison clothing. Her cellmate later claims Leona paid other inmates to do her work for her and also make her bed, iron her clothes and sort her mail. But either way, it seems like Leona's hustling pays off because a little more than a year into her prison stint, she gets her sentence reduced for good behavior. By that time, she's 72 years old

and her husband is in pretty bad health. A judge thinks keeping her in prison for much longer would be, quote, unduly harsh. So in early 1994, after serving just 18 months behind bars, she's released to a halfway house. Then she spends two months on house arrest before returning to her penthouse. She's finally back in the life of luxury.

Helmsley Palace operations have been turned over to a management company, so she has nothing to do but focus on taking care of Harry and completing her court-mandated community service. 250 hours a year for three years. Leona has been given a chance to turn over a new leaf, but old habits die hard. A year after Leona is sprung from prison, she and Harry have settled into their retirement estate.

It's a 10-acre, 20,000-square-foot mountaintop escape in Paradise Valley, Arizona. There's a lagoon pool, another Olympic-sized pool with an underwater sound system, a powder room with 24-carat gold faucets, and of course, staff quarters. Leona has plans for those staffers, too. Plans that go above and beyond their normal housekeeping duties. The staff's dining table is covered in envelopes and small jewelry boxes holding keychains. The task for the maids, the handymen, and the other workers is to wrap the boxes, stuff them in the envelopes, and set them aside for the queen of the manor. And then Leona takes them to the nearby Scottsdale Memorial Hospital as presents for volunteers.

And she'll claim that she wrapped all of them by hand, logging those as her court-mandated community service hours. She is so crazy for this. Just do the hours. You're fine. You can do them. Obviously people found crazy for this. Just do the hours. You're fine. You can do them. Obviously, people found out about this. Yeah, it doesn't take long for it to get out.

One of the pissed off staffers knows just who to call. Leona's old nemesis from the New York Post, Ransdale Pearson. He's at the New York Daily News now, and he breaks the story with a gigantic front page headline. Rotten to the chore. A few months later, the judge in Leona's federal trial rules that she has to perform an additional 150 hours

of community service to make up for what she farmed out to her staff. It's less than the prosecutor asked for, but the judge acknowledges that Leona's spending almost all of her time taking care of Harry these days. But nearly three years after Leona was released from prison, Harry dies of pneumonia at 87. And just like Harry did for Leona when she went to prison, Leona turns off the lights on the Empire State Building.

She's devastated. In a statement, she says, quote, my fairy tale is over. Harry is laid to rest in a mausoleum in New York's Woodlawn Cemetery, next to Leona's son, Jay. His final resting place has stained glass made to look like the Manhattan skyline. Harry left $25,000 to his longtime secretary,

but everything else he left to his beloved Leona. Now she's become the heir to the entire Helmsley Empire. That includes a $1.7 billion personal fortune and one of the largest private real estate portfolios ever, estimated to be worth around $5 billion. At 76, Leona prepares to enter the final period of her life more powerful than ever, but also far more vulnerable. After Harry's death, Leona pours over the condolence letters she's received,

just like how she used to pour over her common cards at the palace. And that's when she discovers a note from a real estate broker named John Cody. Leona has heard his name before. He once visited Dunnellon to talk about a potential business deal. Leona also remembers that he helped another rich widow handle her real estate inheritance a couple decades ago. That detail is especially important now, because Harry's kingdom includes more than 30 million square feet of office space all around the country, as well as apartment complexes and

of course the hotel chain. But Harry had many business partners and who owns what across his entire portfolio is not entirely clear. After a lifetime of worrying people would try and screw her out of what she feels entitled to, Leona wants to hold on to as much as she can. So she decides to give John a call and he seems happy to help. John Cody is in his late 50s. He's a tall, trim man who, if you met him at a party and he said, I'm in real estate, you would say, oh, how nice, and then you would move right along.

Over the next year, he helps Leona settle bitter feuds with Harry's business partners. This clears the way to sell off a gigantic chunk of the Helmsley real estate holdings, like $2.5 billion worth. Leona's happy to part with the ugly office buildings, but she does decide to keep her stake in many of the New York hotels and luxury properties, and of course, her beloved Empire State Building. I mean, listen, you would have to kill me before I gave up the Empire State Building. Well, this isn't the only way John is helping Leona process Harry's death.

He starts accompanying her to social events, out for nice dinners, and even starts teaching her to golf. The rumor mill starts to swirl that Leona and John are doing more than just business together. But she denies it. So does John. He has a wife and three kids. But John must see that Leona is lonely.

Her parkland penthouse is plastered with pictures of Harry. She rarely speaks to her grandchildren, and she has never met most of her great grandchildren. Mostly, she says, because she's mad that none of them are named Harry. John sees that she needs someone to shower with love and affection. So about two years after Harry's death,

he introduces her to the next big love of her life. She's about nine inches tall and eight pounds with big eyes and fluffy white fur. She's a Maltese puppy and her name is Trouble. Trouble becomes Leona's entire personality. She takes her on long walks, gives her a diamond collar, and only serves her chef-prepared meals. Trouble is tiny and sassy, and allegedly, she bites.

Just like mama. You know, I feel like there are so many dog people who are like, I didn't understand love and responsibility until I got a dog. And then I'm like, you interact with so many people in your life, and the first time you're understanding love is because you got a dog. And then I'm like, you interact with so many people in your life, and the first time your understanding love is because you got a dog? Leona's one of those people. It's so troubling.

Well, Leona forbids anyone from referring to her angel as the dog, and instead insists that she be called Princess. She even has trouble star in her own series of ads for the Palace Hotel. But even man's best friend can't replace what Leona's missing, a real man. But when Leona opens her heart to a new romance, she gets a taste of her own bad medicine. I'm Hannah. And I'm Saruti. And we are the hosts of Red-Handed, a weekly true crime podcast. Every week on Red-Handed, we get stuck into the most talked about cases. From Idaho student killings, the Delphi murders, and our recent rundown of the Murdoch Saga. Last year, we also started a second weekly show, Short Hand, which is just an excuse

for us to talk about anything we find interesting because it's our show and we can do what we like. We've covered the death of Princess Diana, an unholy Quran written in Saddam Hussein's blood, the gruesome history of European witch hunting, and the very uncomfortable phenomenon of genetic sexual attraction. Whatever the case, we want to know what pushes people to the extremes of human behavior. Like, can someone give consent to be cannibalized? What drives a child to kill? And what's the psychology of a terrorist? Listen to Red Handed wherever you get your podcasts and access our bonus shorthand episodes exclusively on Amazon Music or by subscribing to Wondry

Plus in Apple podcasts or the Wondry app. In August 2000, a couple of years after Leona sold off much of her empire, she gets an invitation from Joyce Bieber. Joyce is the advertising genius who came up with the Queen of the Palace campaign, the same one who Leona fired after learning she was thinking of doing business with Trump. But now they've apparently reconciled because Joyce is asking Leona to come with her to a small dinner party at a mansion in Miami. Leona accepts. And at that party, she meets a 45 year old optometrist turned businessman named Patrick Ward.

He wows her instantly with his great tan and his big smile, and they hit it off right away, even though they've got a 35 year age difference. They talk for hours, and Patrick seems like a perfect gentleman. He even walks Joyce and Leona to their car at the end of the night. Patrick starts going with Leona to parties. And because this is the only real way to Leona's heart,

they go dancing. Local gossip columns even report that they're spotted kissing at Rita Hayward's Alzheimer's Gala. Patrick also writes her loving notes. Sarah, can you read what one of them says? It says, I care deeply for you and will stand in front of any moving train before I will let that train hit you.

You know, I get the sentiment it's not really written in a romantic way. It's very matter of fact and like honestly quite funny. Yeah, it's really funny. But Sarah, about two months after they meet, Leona names Patrick COO and vice chairman of Helmsley Enterprises. His salary is a cool $400,000 a year. And Leona sells him one of the co-op apartments

she owns on Manhattan's Upper East Side at a massive discount and then she sells him 60 Apartments that she owns in a building on 61st Street again at a more than friends and family rate She even writes him into her will as someone who would help run her estate and her foundation if that isn't romance I don't know what is just two months later though, the real estate broker, tells Leona something that turns her world upside down. Patrick's gay. John had discovered Patrick actually shares a house in Miami with a man. Leona is stunned.

How could someone ever misrepresent themselves to marry into extreme power and wealth? This guy is the winner here. Yeah, it's pretty good. Well, Leona reportedly calls Patrick to her penthouse and confronts him. She tells him the games have got to stop. She wants all of her apartments back. According to Leona, he refuses.

And by the way, Leona later denies that she and Patrick were ever romantic. She says she can't remarry ever because, well, she's too rich. And Patrick later says he never hid his sexuality from her or misrepresented himself. But either way, Leona fires him. Patrick sues for wrongful termination, and that suit is later settled out of court. The flirtation is over. And so is Leona's late- life, Joie de Vivre.

After that, she tells the Wall Street Journal that she's swearing off men forever. But she does promise that her little dog is gonna live well. And this, ironically, will lead to the last great trouble of Leona's life. Shortly after the Patrick scandal, Leona retreats from the spotlight for good. Sometimes she heads off to Dunn-Ellen or to Palm Beach, but mostly she just stays in her

penthouse with her TV shows and her dog. Her priorities are now her dog, herself, and the Park Lane Hotel. In that order. She also starts quietly giving to charity. She gives $25 million to New York Presbyterian Hospital, where Harry got treatment years ago. Immediately after 9-11, she writes a five million dollar check to a fund for police and firefighter widows and children. She funds an animal hospital in New York, and she updates her will so that the majority of her assets are left to a charitable trust which will care for dogs.

On August 20, 2007, Leona dies of heart failure at 87. She's laid to rest next to Harry and Jay in her mausoleum. And by the way, this is a new mausoleum in Sleepy Hollow. Leona got in a fight with Woodlawn Cemetery when they built a public mausoleum next to hers, which blocked her view. Her obituaries discuss her great wealth, her infamous comment about the little people,

and her legacy as the queen of mean. Donald Trump even spares a few kind words. Sarah, can you read what he says in a public statement? Yeah, he goes, Leona Helmsley was definitely one of a kind. Harry loved being with her and the excitement she brought. And that's all that really matters. I mean, pretty crazy considering he spent many years trashing her and hoping for her downfall. Yeah, I mean, he's not known for his consistency,

I suppose. Well, Leona is survived by her brother and her grandchildren and, of course, trouble. But just days after her death, she makes headlines from beyond the grave. Her will reveals that she has disinherited two of her four grandkids for quote, reasons known to them. But she has left $12 million to trouble. Stop, $12 million for the dog? That shouldn't be legal. Dogs can't buy things. Not yet. I just, I hate that so much.

Well, besides a few million for the two grandkids she wasn't beefing with and 10 million to her brother, Leona requests that her entire fortune be left to the Helmsley Charitable Trust, which she wants to focus only on animal welfare. That fortune is more than $4 billion. Her family member, Sue, claiming Leona was mentally unwell when she wrote the will. And ultimately, they reach a settlement that reduces Trouble's inheritance from $12 million to $2 million.

Even the two grandkids Leona tried to snub end up getting a slice of the pie. After Leona's brother refuses to care for Trouble, the dog is sent by private jet to Florida to live with a Helmsley employee. The two live in a secret location with full-time security due to a series of death threats against the dog, which could be a result of Trouble's huge inheritance or the fact that she continues to bite anyone she doesn't like. She lives out the rest of her life in a warm climate and in the lap of luxury. She dies at 12 as one of the wealthiest dogs in the world and maybe the only creature Leona Helmsley never lied to, never stole from, and never cheated out of money.

Sarah, do you love rich dogs now? How on board are you with giving your all your money to a dog? A tiny white dog that's biting everybody. I have so many questions about how that works. Like forget that I think it's so wrong. But like this dog was given two million dollars and someone who worked for her used that money to take care of the dog and themselves. Like is that kind of the arrangement here? Does someone like come around and check in and is like, okay cool you're using that two million dollars for the dog the way that is written in the law. I don't know.

It just, it doesn't really make much sense to me. Basically she just threw away money, right? Out of spite. Yeah. I think she just feels like if things don't go exactly her way, she will punish you. And the only creature in her life who did everything she ever wanted, I guess, was Harry, but he's gone. And now this dog that can't speak English.

I mean, everything about this woman was terrible from tip to tail. Do you feel like you learned anything about how to be a woman in business from Leona? Yeah, I think she was really kind of evil and terrible, and that's how she got to the top. Like, that's how she got her first big job. So I think maybe she really kind of evil and terrible, and that's how she got to the top. Like, that's how she got her first big job. So I think maybe she realized, like, well, no matter what I do,

people will always see me as this awful bitch, so may as well be one. Interesting. Interesting. I really do think she saw herself as like the world's victim and underdog, and that's why she felt so righteous in all the terrible things she did. I actually think she was so unwilling to view herself as a victim, like in her younger life,

that she insisted on becoming an antagonist. Like I think she knew that there were things about her upbringing that were unfortunate. She grew up poor. I think she didn't like that and she was uncomfortable with it. And so she did what I think a lot of people do when they grow up with bad circumstances, is they say, I'm just going to rage at everybody until I get everything that I want because I have suffered and I've suffered so much that I deserve it all. I think what enables people like her and like so many of the rich people we cover is that the system kind of lets them be bad for a certain amount of time until

one of them becomes the example that has to be made. And it was Leona because she was terrible to everyone. But what she was doing wasn't that different from other rich people. She was just kind of like, I'm not doing anything wrong. I shouldn't be paying taxes. I should be using company money to build my weird mansion and estate because that's my money. You know what I mean? Like I think she's very bold with the disregard she had for the rules of the world. Yeah, and it just seems like the public was very primed to hate her and some of that for totally deserved reasons because she sucked

and then some of it just because she was like a woman and she was annoying. Yes. I kind of wish that we got to live in a world where Leona was alive for Trump to run for office because I don't think she would have stopped him, but I do think I would have appreciated watching like a mean bitch from the 80s just scream at him. Think about Leona having Twitter. That would have been so good. I know. And it's interesting to see this kind of reaction to Leona

because the world had never seen something like this before. And now someone like Leona is kind of relatively normal, like a billionaire who you can't stop seeing everywhere. She was a trailblazer for annoying billionaires. I'll say that. Yeah, I guess we have to admire her because she's a woman. Like, to be a woman and awful as she was a renegade. They didn't have a lot of those back then.

Now we're a little more used to women being the worst and being shrewd capitalists and like stealing money from people. But back then there weren't a lot of them. She kind of got everything she wanted as well. When you think of it, like I'm sure she was miserable, but she didn't go to jail for that long and she ended up leaving prison and still being extremely wealthy. And maybe she wasn't happy, but she stayed rich. I want you to know that when I die I'm giving all my money to my cat and you

will have to take care of her. But I'm gonna make you both live in squalor. Why would I do that? You can't make me do that. Um, it's the law. Sorry. I don't make the rules. I just enforce them. Tell us about yourself by completing a short survey at wondery.com slash survey. This is the art of the steel part two. I'm Saatchi Cole. And I'm Sarah Haggit. If you have a tip for us on a story that you think we should cover, please email us at

scamfluencers at wondery.com. We use many sources in our research. A few that were particularly helpful were The Queen of Mean by Ransdale Pearson, Helmsley's The Rise and Fall of Harry and Leona by Richard Hammer, and Palace Coup, the inside story of Harry and Leona Helmsley by Michael Moss. Colleen Scriven wrote this episode. Additional writing by us, Sachi Cole and Sarah Hagge. Sarah Eni is our story editor and producer, and Eric Thurm is our story editor.

Fact-checking by Meredith Clark. Sound design by James Morgan. Additional audio assistance provided by Adrian Tapia. Our music supervisor, Iskaaf Alaska, is for Freeze On Sync. Our managing producers are Desi Blaylock and Matt Gant. Janine Cornelo and Stephanie Jens are our development producers. Our associate producers are Charlotte Miller and Lexi Peary. Our producers are John Reed, Yasmin Ward, and Kate Young.

Our senior producers are Jenny Bloom and Jen Swan. Our executive producers are Jenny Lauer Beckman, Marsha Louie, and Erin O'Flaherty. For Wondry. In the climate ravaged year of 2072, the city of Pura stands as a miraculous green haven, a geo-engineered paradise that protects fortunate residents from the global catastrophes of heat domes, fires, floods and droughts. Demetria Lopez heads up Pura's public relations, tirelessly promoting the city's idyllic image. But when she stumbles upon a dark secret that if exposed would be the downfall of Pura's existence, she must decide who and what she is willing to protect.

From Wondery, the makers of Academy and Dr. Death, The Last City stars actors Reyes Seahorn, Jeannie Tirado and Maury Sterling. Follow The Last City on the Wondery app or wherever you get your podcasts. You can binge all episodes of The Last City early and ad-free right now by joining Wondery+.